Citation: Xue-Dong Zhang, Na Gao, Zhi Guan, Yan-Hong He. Enzyme-catalyzed asymmetric domino aza-Michael/aldol reaction for the synthesis of 1,2-dihydroquinolines using pepsin from porcine gastric mucosa[J]. Chinese Chemical Letters, ;2016, 27(6): 964-968. doi: 10.1016/j.cclet.2016.02.013 shu

Enzyme-catalyzed asymmetric domino aza-Michael/aldol reaction for the synthesis of 1,2-dihydroquinolines using pepsin from porcine gastric mucosa

Key Laboratory of Applied Chemistry of Chongqing Municipality, School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, China

Received Date: 7 September 2015
Revised Date: 11 January 2016

Fund Project: This work was financially supported by the National Natural Science Foundation of China (Nos. 21276211 and 21472152).

An unprecedented enzyme-catalyzed asymmetric domino aza-Michael/aldol reaction of 2-aminobenzaldehyde and α,β-unsaturated aldehydes is achieved. Pepsin from porcine gastric mucosa provided mild and efficient access to diverse substituted 1,2-dihydroquinolines in yields of 38%-97% with 6%-24% enantiomeric excess (ee). This work not only provides a novel method for the synthesis of dihydroquinoline derivatives, but also promotes the development of enzyme catalytic promiscuity.
- Pepsin,
- Biocatalysis,
- Domino aza-Michael/aldol reaction,
- 1,2-Dihydroquinolines,
- Enzyme catalytic promiscuity
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